Bet On Yourself isn’t for the ones who already made it, it’s for the ones who feel hesitant to start. Hosted by entrepreneur and author Angelo “Gege” Pitirri, this show dives into real stories of risk, resilience, loss and rebuilding. From failure to success, Angelo shares honest lessons on turning hesitation into belief and doubt into drive, inspiring you to finally make your own bet on yourself.
OBSESSION: Prision, Passion & Reinvention | Karim Baratov | Bet on Yourself S3:E2
What does it take to rebuild your life from the ground up after losing everything? In Season 3, Episode 2 of the Bet On Yourself Podcast, Angelo “Gege” Pitirri sits down with Karim Baratov for an unfiltered conversation about OBSESSION: Prison, Passion & Reinvention.
Karim opens up about navigating the darkest chapters of his life, the relentless drive required to survive, and how he channeled that intense obsession into a powerful comeback and reinvention. If you’ve ever faced rock bottom and wondered how to rewrite your story, this episode is a masterclass in resilience.
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CONNECT WITH ANGELO “GEGE” PITIRRI
🌐 Website: https://angelopitirri.com
📸 Instagram: @angelopitirri
BET ON YOURSELF PODCAST
📸 Instagram: @thebetonyourselfpodcast
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👕 Bet On Yourself Merch: https://betonyourselfstore.com
TIMESTAMPS
0:00 — Introduction: The Power of Obsession
3:15 — The Turning Point: Facing Reality
12:40 — Inside Prison: Survival and Mental Fortitude
25:10 — The Breaking Point vs. The Breakthrough
38:05 — Reinvention: Building a New Future From Scratch
52:30 — Final Advice on Betting on Yourself
#BetOnYourself #KarimBaratov #Podcast #Reinvention #Resilience #AngeloPitirri
18 Aug 2026
ZERO EVIDENCE: UFC Fighter Serhiy Sidey on Believing Before You Have Proof | Bet On Yourself S3:E1
What if you just knew you were going to make it, even when you had ZERO EVIDENCE to prove it?Season 3 of Bet On Yourself begins with UFC bantamweight Serhiy Sidey.Serhiy sits down with Angelo “Gege” Pitirri for a deeply personal conversation about belief, adversity, loss, fear and what it actually takes to bet on yourself when life doesn't go according to plan.But one of the most powerful parts of this conversation wasn't planned at all.Serhiy opens up about being bullied as a kid and being genuinely afraid of confrontation. That fear helped lead him to a martial arts gym and ultimately down a path that would take him all the way to the UFC.Years later, Serhiy has worked with kids who walked into martial arts gyms for the exact same reason he did: they were being bullied. He talks about what those kids are really looking for, how martial arts can build confidence without creating aggression, what parents can do to help, and why some of the toughest people he's met are also the kindest.The conversation also takes us inside Serhiy's fighting career from Dana White's Contender Series and his arrival in the UFC to the devastating injury that cost him the opportunity to fight at Madison Square Garden.He opens up about losing his father, the importance of his fiancée Sarah, turning losses into growth, fighting through self-doubt and imposter syndrome, and the mentality he uses when the cage door closes.And then comes the moment that gave this episode its name.Serhiy explains that even at 16 years old, he had this strange voice in his head telling him he was going to make it.He had zero evidence to support it.He just knew.That's Bet On Yourself.Season 3 • Episode 1ZERO EVIDENCESubscribe for new episodes of the Bet On Yourself Podcast.CONNECT WITH ANGELO “GEGE” PITIRRI🌐 Website: https://angelopitirri.com📸 Instagram: @angelopitirriBET ON YOURSELF PODCAST📸 Instagram: @thebetonyourselfpodcast▶️ YouTube: @BetOnYourselfPodcast 👕 Bet On Yourself Merch: https://betonyourselfstore.com0:00 Zero Evidence0:41 Season 3 Begins1:21 The Injury & Road Back to the UFC4:11 Dana White’s Contender Series5:35 The Controversial UFC Loss8:01 Proving He Belongs in the UFC11:42 Coming to Canada From Ukraine15:19 The Madison Square Garden Dream Ends19:07 His Father’s Final Words29:26 Turning Loss Into Growth32:38 ZERO EVIDENCE: Betting on Yourself45:42 From Being Bullied to Becoming a UFC Fighter49:28 What Serhiy Would Tell a Bullied Kid55:08 Who Does Serhiy Want Next?
23 Feb 2026
Bob May: Accepting the Results, Betting On Yourself (Season 2 Episode 3)
What happens when you bet on yourself…work harder than anyone else…and still feel like you didn’t reach your own expectations?In this episode of Bet On Yourself, former PGA Tour professional Bob May opens up in one of the most honest conversations of his career.From being the #1 junior golfer in California…to winning internationally…to competing in the final group at a major championship against Tiger Woods at the 2000 PGA Championship…This conversation goes far deeper than golf.It’s about identity.It’s about pressure.It’s about regret.It’s about learning to accept the result even when it doesn’t match the dream.Bob reflects on:• Growing up outside the traditional golf pipeline• Being coached with negative reinforcement• Losing confidence in college & dealing with Dyslexia• The mental battle of competing at the highest level• The emotional aftermath of taking Tiger Woods to a playoff at Valhalla• Living with unmet expectations• Redefining success beyond trophiesThis isn’t a highlight reel interview.It’s a raw conversation about what it really means to bet on yourself — and what happens when the outcome doesn’t look the way you imagined.If you’ve ever worked your entire life toward something and still felt like it wasn’t enough… this one will hit home.0:00 – “I Worked So Hard… And Never Did”1:05 – The #1 Junior Golfer in California4:40 – Beating His Coach 150 Times6:30 – Playing Arnold Palmer as a Young Pro9:00 – Respect vs Arrogance on Tour12:00 – Negative Coaching & Lost Confidence17:00 – Elite Ball Striking Philosophy29:00 – Did I Live Up to My Own Expectations?30:55 – Winning on the European Tour33:00 – Competing at the Highest Level38:40 – The Playoff at Valhalla41:00 – Regret, Identity & Acceptance48:30 – Success Beyond Trophies55:40 – Advice for the Next Generation#BetOnYourself#BobMay#TigerWoods#pgachampionship #mindsetshift #Valhalla#GolfPodcast#Mindset#Resilience#PersonalGrowth#HighPerformance
16 Feb 2026
Jasmine Jasudavicius on Sacrifice, Loss, and What It Really Takes to Fight in the UFC. Season 2 EP2
In this conversation, Jasmine Jasudavicius opens up about the real cost of chasing greatness physically, mentally, and emotionally.We talk about:Starting MMA later than mostFear and nerves before walking outFighting through pain and injuryLosing in front of your countryThe pressure of being a woman in a brutal sportSacrifice, humility, and resilienceand what it truly means to Bet On YourselfWhat makes this episode special is how natural and honest the conversation is especially considering Jasmine and Angelo had just met before sitting down.This isn’t a hype interview.It’s a real conversation about discipline, loss, and choosing to keep going.🎙 Season 2, Episode 2Watch & Subscribe: / @betonyourselfpodcast (https://www.youtube.com/channel/UCC19BZIz896ClcJj0qX-wJw)Shop the collection: www.betonyourselfstore.comOfficial site: www.angelopitirri.comCoaching: www.betonyourselfcoaching.comProdigy Personnel: www.prodigypersonnel.com0:00 (https://www.youtube.com/watch?v=Y-yD-vksWWM) – It’s time0:36 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=36s) – Giving up tickets & why the moment mattered1:23 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=83s) – How the podcast started from loss2:48 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=168s) – Bankruptcy, poker, and betting on yourself4:59 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=299s) – Business vs fighting: control & competition6:40 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=400s) – How Jasmine found MMA at 268:50 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=530s) – First sparring, first fights, falling in love with it10:45 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=645s) – Turning pro & early nerves12:20 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=740s) – Fear before walking out13:50 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=830s) – Being smaller, proving yourself15:26 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=926s) – Tunnel vision, losses, and learning the hard way16:22 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=982s) – Carrying the weight of Canada18:25 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1105s) – Neutral thinking, grief, and loss20:08 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1208s) – Family after a loss22:19 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1339s) – Life after fighting23:37 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1417s) – Growth of women in MMA25:46 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1546s) – Training vs the fight27:49 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1669s) – Hardest skills to learn28:47 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1727s) – Advice to young athletes31:48 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=1908s) – Who shaped Jasmine’s mindset33:44 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2024s) – Cardio, emotion, and fatigue36:13 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2173s) – Respect after the fight37:06 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2226s) – A full training camp breakdown39:44 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2384s) – Living in pain as a fighter40:14 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2414s) – Being a woman in the sport41:04 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2464s) – Fighting with a broken orbital44:28 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2668s) – Championship goals46:14 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2774s) – Life as a contender47:34 (https://www.youtube.com/watch?v=Y-yD-vksWWM&t=2854s) – What betting on yourself really meansCredits:Produced & Edited by Noah Bollert (@noahbollert)Sound & Set by Noah Bollert (@noahbollert)Behind the Scenes by Mario McLennon (@mclennon_22)
16 Feb 2026
Jasmine Jasudavicius
We talk about:Starting MMA later than mostFear and nerves before walking outFighting through pain and injuryLosing in front of your countryThe pressure of being a woman in a brutal sportSacrifice, humility, and resilienceand what it truly means to Bet On Yourself
7 Nov 2025
PART B JACK LENZ BET ON YOURSELF
Canadian icon Jack Lenz discusses his Baháʼí faith and how it inspires his art and supports his work in human rights, women’s equality, and unity across cultures in an interview with Angelo Pitirri.
6 Nov 2025
Jack Lenz: The Heart: Grief, Gratitude & Story Behind ‘OK Blue Jays’ | Bet On Yourself Podcast.
Host Angelo Pitirri interviews composer Jack Lenz about grief, gratitude, and the story behind the iconic "OK Blue Jays" anthem, revealing how he transforms anxiety into purpose and art into legacy.
18 Jul 2025
Winning Friendships, Real Bets & The Power of Showing Up | Bet On Yourself Podcast
Angelo Pitirri and friends discuss competition, friendship, and accountability, exploring how challenges build confidence and genuine relationships foster success in both personal and professional spheres in this roundtable interview.
10 Jul 2025
The Grad-Girls vs Boys Part A “The Broads” 6 Teen Girls on Identity, Sports, Loss, Life & Religion
Angelo Pitirri hosts six teenage girls, including Jessica Pitirri, in an interview episode, as they explore identity, mental health, relationships, and faith, offering insights into the challenges and triumphs of growing up.
17 Jun 2025
Accept the Mirror When Shown: Rebrand, Rebuild & Inject Confidence | Ep. 4 w/ Nurse Rebecca
Angelo Pitirri interviews Nurse Rebecca about rebranding one's identity, removing negative influences, and showing up confidently, revealing mindset shifts and the emotional impact of personal transformation.
2 Jun 2025
Episode 3 — $300K Invested. COVID Hit. Banks at Her Throat. | Chelsea Spencer on Bet On Yourself
Coach Chelsea Spencer discusses with host Angelo Pitirri risking everything to build a business, facing COVID challenges, and discovering worth through community, coaching, and belief in this interview episode.
23 May 2025
Episode 02: Bold Design, Risk-Taking, and Building a Business in Muskoka
Christina Carr, founder of CC Interiors, discusses building a creative business in Muskoka and making brave choices in design, which redefines success for women, in this interview with Angelo Pitirri.
15 May 2025
Episode 01: Getting To Neutral
From pro poker to Prodigy Personnel. From bottomed out to building a $50M firm. In this premiere episode, Angelo Pitirri opens up like never before. You’ll hear the real, gritty version of his journey: the wins, the walls, and the wake-up calls that forced him to level up—personally and professionally. From managing CRA audits and back-end chaos to honouring his sister’s legacy with a life insurance payout no one saw coming, this episode is a behind-the-scenes look at the moment when betting on yourself isn’t inspirational—it’s survival. Jeff Welsh, long-time friend and fellow entrepreneur, joins Angelo for an unfiltered conversation that hits on what it means to get to neutral—to remove ego, emotion, and expectation, and just take the next right step forward. Topics Covered: Angelo’s early business mistakes—and how he bounced back. The pressure of going all-in with no fallback plan. Why neutral thinking saved his mindset. Compliance, CRA letters, and the sh*t no one prepares you forHow one conversation in Vegas changed everything. Quoting Trevor Moawad’s It Takes What It Takes, Angelo lays out the mental frameworks that helped him grow through chaos—and gives tactical advice for new founders trying to do the same. Want the book “It Takes What It Takes” but can’t afford it?
Angelo’s buying. Just message him: angelo@angelopitirri.com. This episode is more than a backstory—it’s a blueprint for what betting on yourself actually looks like when you’re under pressure, underfunded, and still find a way. #BetOnYourself #Entrepreneurship #StartupStories #NeutralThinking #BusinessGrowth #AngeloPitirri #PodcastLaunch #RealBusinessTalk #FounderLife
18 Apr 2025
Episode Zero
In this launch episode, host Angelo Pitirri shares the raw, inspiring story behind the Bet On Yourself podcast. From an unexpected childhood uprooted by divorce to overcoming personal bankruptcy, and ultimately building a $50 million staffing firm, Angelo opens up about the defining moments that shaped his journey.
This episode sets the tone for what's to come: real conversations about entrepreneurship, resilience, relationship-building, and yes — a few tips and tricks for navigating Vegas like a pro. You'll hear about Angelo's early lessons in business, his pivot from professional poker to running a successful company, and his deep belief that betting on yourself is the ultimate investment.
Future episodes will bring on guests ranging from NHL players like James Wisniewski to sports betting experts, entrepreneurs, and everyday risk-takers who have defied the odds. If you're ready to turn setbacks into setups and build a life on your own terms, this podcast is for you.
Subscribe, follow, and get ready to Bet On Yourself.
Who has been a guest on Bet On Yourself with Angelo Pitirri
Names identified in recent episode analyses. Showing up to five guests.
Jack Lenz
friends
Jessica Pitirri
Nurse Rebecca
Chelsea Spencer
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
358,561
Score snapshot 15 Sept 2025
Spotify
5.0 / 5
5 ratings
Podcast Authority Score: 32 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
30
Social presence
0
YouTube
86
Engagement
0
Contact Bet On Yourself with Angelo Pitirri
Guest appearances
Does not typically book guests
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Angelo Pitirri host the show. Published by Angelo Pitirri.
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